Trifluoroacetic acid → 4-((5,6-Dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acid

HRID 512040Notes

Reaction equation

HRID 512040 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:23]([F:24])=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([F:25])[CH:12]=2)[CH:5]=[N:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:23]([F:24])=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:25])[CH:12]=2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86682568tert-Butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate

Product 1

HCID 866825694-((5,6-Dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate (Preparation 13, 490 mg, 1.27 mmol) in DCM (5 mL) was added TFA (5 mL). After 30 minutes the reaction mixture was concentrated in vacuo and the resulting residue was purified by reverse phase chromatography eluting with H2O/MeCN/HCOOH (95/5/0.1 to 5/95/0.1, Biotage™ 40 g C18-silica gel) to yield the title compound (210 mg, 50%).

Workup

  1. concentrationAfter 30 minutes the reaction mixture was concentrated in vacuo
  2. customthe resulting residue was purified by reverse phase chromatography
  3. washeluting with H2O/MeCN/HCOOH (95/5/0.1 to 5/95/0.1, Biotage™ 40 g C18-silica gel)

Sources & evidence

ORD record
ord-f00bce9fb69e490a853813c9741f2d31
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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